After more than 20 years as an actor, 38-year-old Leonardo DiCaprio is still one of Hollywood's and most eligible bachelors. And after dating Gisele Bundchen, Bar Refaeli and Erin Heatherton, he's also one of Hollywood's biggest modelizers. (Of course, he made an exception for Blake Lively -- but who could blame him?)
Kate Upton: If Leo wants to continue his model streak, why not go for Sports Illustrated covergirl Kate Upton? She's curvy, sexy and has some killer dance moves. And even though she may be casually dating baseball star Justin Verlander, we think Leo could easily distract her.
Rihanna: She shines bright like a diamond, he starred in Blood Diamond -- so at the very least, they've got precious stones to talk about! RiRi was briefly linked to Leo in 2008, and four years later, the wild child could be just what he needs to keep his attention. And while she's not a runway model, she did just share the catwalk with the world's best, so that's gotta count for something!